Methysticin

Base Information

• Chemical Name: Methysticin
• CAS No.: 495-85-2
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.273
• UNII: M832AIJ6HX
• ChEMBL ID: CHEMBL579224
• DSSTox Substance ID: DTXSID5033674
• Metabolomics Workbench ID: 70329
• Nikkaji Number: J6.085B
• NSC Number: 112158
• Wikidata: Q3333720
• Wikipedia: Methysticin
• Mol file: 495-85-2.mol

Synonyms:methysticin;methysticin, ((E)-(+-))-isomer

Chemical Property of Methysticin

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 5.39E-10mmHg at 25°C
• Melting Point: 139-140.5 °C
• Refractive Index: 1.597
• Boiling Point: 496.5 °C at 760 mmHg
• Flash Point: 224 °C
• PSA: 53.99000
• Density: 1.31 g/cm³
• LogP: 2.27430
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 274.08412354
• Heavy Atom Count: 20
• Complexity: 428

Purity/Quality:

99%, ^*data from raw suppliers

Kavatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=O)OC(C1)C=CC2=CC3=C(C=C2)OCO3
• Isomeric SMILES: COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3
• Uses: A lactone isolated from the Kava plant (Piper methysticum). A lactone isolated from the Kava plant (Piper methysticum). The active constituents of Kava are a group of approx. 18 compounds collectively referred to as kavalactones or kava pyrones. One of the active components of the intoxicating beverage Kava from the Pacific Islands.

Technology Process of Methysticin

There total 13 articles about Methysticin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one (1092383-57-7) + 3,4-(methylenedioxy)benzenediazonium tetrafluoroborate (1682-37-7) → (+/-)-methysticin (495-85-2,6581-44-8,20697-20-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium acetate; In benzonitrile; at 100 ℃; for 1h; stereoselective reaction; Microwave irradiation;

DOI:10.1021/ol901416e

Reference yield: 44.0%

5-iodo-1,3-benzodioxole (5876-51-7) + (R)-6-((E)-2-(tributylstannyl)vinyl)-5,6-dihydro-4-methoxypyran-2-one → (+)-methysticin (495-85-2)

Guidance literature:

With trifuran-2-yl-phosphane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; at 115 ℃;

DOI:10.1021/ol0493960

Reference yield: 42.0%

4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one (1092383-57-7) + 5-iodo-1,3-benzodioxole (5876-51-7) → (+/-)-methysticin (495-85-2,6581-44-8,20697-20-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 - 150 ℃; for 0.0916667h; Microwave irradiation;

DOI:10.1016/j.tetlet.2008.07.102

upstream raw materials:

5-iodo-1,3-benzodioxole

methyl 4-bromo-3-methoxy-2-butenoate

(E)-3,4-methylenedioxycinnamaldehyde

4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one

Downstream raw materials:

(+/-)-dihydromethysticin

(+)-dihydromethysticin

7-benzo[1,3]dioxol-5-yl-3-methoxy-hepta-2,4-dienoic acid

3,4-Dihydroxybenzoic acid

Refernces

• 1、 Soldi, Cristian,Moro, Angelica V.,Pizzolatti, Moacir G.,Correia, Carlos R. D.. "Heck-matsuda arylation as a strategy to access kavalactones isolated from polygala sabulosa, piper methysticum, and analogues". experimental part. p. 3607 - 3616. Retrieved 2012/07/31.
• 2、 Moro, Angelica Venturini,Cardoso, Flavio Sega Pereira,Correia, Carlos Roque Duarte. "Highly regio- and stereoselective Heck reaction of allylic esters with arenediazonium salts: Application to the synthesis of kavalactones". supporting information; experimental part. p. 3642 - 3645. Retrieved 2011/02/25.